The GenX Delimma
Interview by Jennifer Cooper
“I wanted more, and for a long time, I thought I was abnormal for feeling that way.”
If you are a Gen Xer, you are the “lost generation,” the “latchkey kid” generation, the generation that was called “slacker” even though you worked just as hard as everyone else. Sure, that stereotype was cute in Clerks, but in real life? It didn’t exist. Just like the stereotypes of Millennials spending all their money on avocado toast and fancy coffees. Sure, that’s the real reason people don’t have economic stability these days.
And while every generation has their own issues, challenges, and celebrations, when you’re stuck in the middle, you’re fully aware that you’ve got one foot on either side of epic and seismic shifts we’re all experiencing, especially in the way we work.
As I do my own deep dive into the work of unlearning some of the really toxic stories society told us about womanhood, I’ve discovered the profound and expansive joy of finding others who are also on this journey. We’re choosing collaboration over competition, love over fear, and evolution over status quo.
One of these people is Jen Wilson. Jen says growing up she always felt like the odd one out. She played the “good girl game” until, like so many of us, she was crushed by the weight of it. Now she’s helping others pursue their passions and turn their business dreams into reality. I recently spoke with her about the challenges we face in midlife and why understanding your purpose is a key to success.
You mostly coach women in midlife. What do you find is one of the biggest challenges we face when it comes to mindset?
As Gen Xers, we're the generation sandwiched in between the baby boomers and Millennials, which means we have one foot in the old, traditional way of looking at work, careers and jobs, and the other foot in the new way. The new way is more about satisfaction at work and the job you do, versus strictly pay and benefits.
This means that tradition, expectations, and obligation can still have a stronghold on our way of thinking, and it can be hard to break free from that. And since many of us are surrounded by people in our generation who aren’t comfortable with the “new way,” we accept where we are: stuck. When I think about my parents, there was never ever any conversation about passion or being happy with your job. A job was simply a means to an end. They went to work every day, had vacation and health insurance, bought a house, put me through college, and retired after 30+ years with the Federal Government...and they were happy.
But I wanted more, and for a long time, I thought I was abnormal for feeling that way.
To answer your question, the biggest challenge with mindset is believing in the possibility that you can live the life you dream of, and that you’re not self-absorbed or a weirdo for wanting more than what society told you was enough.
Also, women are givers and we often put ourselves last. But I want women to know that it’s possible and it’s ok—you have permission to go for it. It’s possible to define your own worth, do work that matters, and write your own life story. It’s possible to pursue a path that no one else you know is on. It’s possible to be an example to your kids—to show them what it looks like to really go after your dreams without feeling like you’re betraying your 9-5 or your family.
What role does imposter syndrome play in stopping people from launching their own business, especially if they have kids or a 9-5?
Imposter syndrome is one of the biggest roadblocks getting in the way of women launching their own business.
Our identities are entrenched in “what we do.” We’re a “Senior VP” or “Marketing Director” and after we have kids, we become “Mom,” and we can easily get lost in these identities.
There are plenty of skills we develop in Corporate or as a parent that are hugely valuable, but it’s not everything you need to be a successful entrepreneur. When you work for Corporate, you have goals, job descriptions, KPIs and “best practices” and they’re all set by Corporate. As an entrepreneur, there aren’t any employment manuals or anyone to tell you what to do next, and that’s scary. So our brains incorrectly tell us that we can’t (and shouldn’t) launch our own business, and we believe it.
The voice in our heads warns us that we don’t have the necessary experience or expertise and that we’ll fail, or we'll be neglecting our kids if we do this. And we tell ourselves that we should be happy and content with our Corporate titles and with being a Mom. Those thoughts are the root of imposter syndrome. They hold us hostage, keep us small, but most of all, they are a complete fallacy.
Imposter syndrome is so powerful that you need to battle it or it’ll win and stop you short every single time. Instead of automatically defaulting to your work and “mom” identity, adopt a new identity you are an entrepreneur who proudly works a day job and is present for your family. Try that on instead!
You’ve tried a variety of different creative or entrepreneurial pursuits over the years—I often think there’s a lot of overlap between the two—what’s one of the biggest lessons you’ve learned from them?
The number one lesson I learned is that purpose matters in your business, no matter what type of business you dream of. When you’re the Captain of your own ship, having direction and a destination matters. I talk a lot about this in the next question, so if I’d like to offer one additional thought: surround yourself with the right people.
When I first started, I had two things working against me: (1) I felt like I had to do everything myself and was too proud to ask for help or advice, and (2) I was hiding. That wasn’t exactly a recipe for success, and I struggled.
It took years of mindset work, and even then, I had to force my introvert self to engage with other entrepreneurs. I was afraid of being judged. My mind told me that I didn’t have a “real” business since it was part-time, I didn’t have a big network, I was moving so slowly, and (gasp!) I didn’t have all the answers. But I quickly realized that all of that was in my head, because almost no one has all the answers or a giant network to start. And, my fear of being ostracized was ridiculous because most people are decent and kind and would never intentionally try to make me feel bad about myself.
It wasn’t them, it was me.
Once I figured that out, I was determined to meet more people. I joined networking groups and started asking people to join me for virtual or in-person coffee dates. And wouldn’t you know--building relationships and surrounding myself with good people is one of the main reasons my business is on an upward trajectory. Not only is my business growing, but being with people who understand the journey I'm on, who don’t think I'm crazy when I speak my dreams out loud, who are willing to bounce ideas around, and make me feel less alone, is worth way more than money.
“When I first started, I had two things working against me: (1) I felt like I had to do everything myself and was too proud to ask for help or advice, and (2) I was hiding. That wasn’t exactly a recipe for success, and I struggled. ”
You talk about why purpose matters in business. Why does it?
When you don’t know what your purpose is, or the reason “why” you do what you do, you’re captaining a ship with no specific destination or direction.
For example, when you tell someone to run a report and create a spreadsheet with specific numbers, it’s tedious. But if you tell them the purpose is to use the spreadsheet in a presentation that might win them business and save jobs, the task feels completely different. There’s a reason for the spreadsheet—a clear and compelling purpose, which gives them the fuel to get the work done.
Knowing your purpose, or “why you do what you do” is incredibly important. Your purpose is your foundation—your anchor. It’s your North Star that provides guidance in decision making and informs the type of business you design. It helps you do the tedious things and the hard things and helps you power through obstacles and setbacks.
And without knowing your purpose, you might end up with a business that isn’t congruent with who you are at your core.
As a real-life example, my purpose is to help people choose to live a life on purpose and with purpose. This is why helping women launch and grow their businesses fulfills my purpose, and why selling on eBay, even though I was making money, simply didn’t cut it. It’s also the reason why at my previous 9 to 5, I grappled with mental and emotional issues which manifested itself physically because what I did every day didn’t align with my purpose.
As humans, we’re wired to do everything in our power to appear and be consistent with our beliefs. If you’re pursuing a job, career or business that’s inconsistent with your core beliefs, there will always be a disconnect and you’ll likely feel unfulfilled and unhappy. I’ve been there.
So, know your purpose and vision for your life, and ensure your business “fits” into that big picture.
Between juggling a 9 to 5 with a side business yourself, what’s your self-care practice?
I wish I could say I had some elaborate and luxurious self-care practice, but in reality, my outlet is pickleball. I’m so glad I went outside of my comfort zone to start taking lessons. It’s quickly become an obsession. it’s fun and I get to exercise and meet new people at the same time!
Huge thanks to Jen for being here. Did you also see yourself when she talked about the two things she had working against her: being too proud to ask for help and hiding? If you didn’t, I sure did. I felt SEEN and not in a good way.
It reminds me how many of us feel these ways and yet, we’re not always able to talk about it because we’re either not given the space or because we feel guilt or shame for feeling them. That’s conditioning many of us grew up with that we still wrestle with today. And it’s more than time to let go of it. So, here’s to PURPOSE, passion, and throwing your arms fully around the vision you have for your life and giving it all the love!
You can learn more about how you can work with Jen on her site, connect with her on LinkedIn, and follow her on Instagram. She’s a joy to have in your feed!
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